


His Boy

by Sunehri_c



Category: Gilmore Girls
Genre: Anal Fingering, Daddy Kink, Dean Is Whipped, Dean has a big dick, Dean is a Sweetheart, Dirty Talk, Gay Sex, M/M, Masturbation, Mutual Masturbation, Phone Sex, Size Difference, Top Dean, bottom reader
Language: English
Status: Completed
Published: 2020-12-21
Updated: 2020-12-21
Packaged: 2021-03-10 23:08:25
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,498
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28215243
Author URL: https://archiveofourown.org/users/Sunehri_c/pseuds/Sunehri_c
Summary: Y/N’s new in town. Dean takes a liking to the boy. What started off as an innocent phone call lead to some not-so-innocent events.
Relationships: Dean Forester/Male reader
Kudos: 11





	1. Call Me Maybe

Moving from a big bustling city to a small, unheard of town in the middle of nowhere certainly wasn’t easy. This you knew for sure after your mom announced you’d be moving to Stars Hollow, Connecticut. You hadn’t known what to expect, having lived the life of busy streets and skyscrapers since you were born. 

What would it be like? A desert with broken down houses and tumbleweeds? A ghostown blanketed in permanent silence? You really, really weren’t keen on the decision. To your surprise, however, it was quite the opposite of what you’d envisioned. Stars Hollow had a nice, homely feel to it. It wasn’t New York, but there was a decent amount of people on the streets and cars on the road. The leaves grew crisp in the grasp of autumn, drawing patterns in the breeze. 

The townspeople were unbelievably welcoming, making sure you felt like one of them already. With the Halloween celebrations taking place, there wasn’t one second of boredom to spare. Luke’s had essentially become your second home. Life was good. 

This takes us back to present time, as you’re currently heading towards the local grocer. Your mom had some errands to run for the day, so she put you in charge of groceries. A soft jingle rang throughout the store as you pushed the door open. You were greeted with a smile from the cashier and a quick “good afternoon” while he was bagging vegetables. You gave a small nod, taking in his appearance for a moment. ‘Cute’, you mused to yourself. He was a brunette, standing at 6ft at least. Definitely your type. But you tore your focus away from him onto the list you were holding.

Bidding his last customer goodbye, Dean found his eyes tracing back to your form wandering between the aisles. You were unaware of his gaze as you hummed softly to the jazz music playing from the speakers. He wondered why he’d never seen you around before. You looked about the same age as him. He found you... pretty. Could a boy be pretty? Well Dean figured you could give female models a run for their money. 

He was so lost in his thoughts he didn’t notice you coming up to him until he felt a light tap on his shoulder. “Excuse me, can you help me find the cinnamon please?” You asked politely. “Sure thing, follow me.” You paced behind him as he led you to one of the back aisles. “Right up there.” He pointed to the boxes stacked on an abnormally high shelf. “Um... Could you get it down for me?” You flushed in embarrassment. Dean chuckled a little, finding it adorable how tiny you were. “Here,” he placed a box in your hands. You thanked him, about to go to the checkout but he stopped you. “Wait, I don’t think I’ve seen you in town before. Are you new?” he asked. “Yup. I moved here a couple days ago from New York City.”

“New York! Jeez, that’s pretty far from here.”  
“Mhm, my mom wanted a fresh start. Said life will be better once she finds a new job and I settle in to a different school.”  
“Stars Hollow High. I’m starting next week.” You smiled. “Oh same here! You know, if you need someone to show you around...”  
“I’d appreciate that,” you paused, scanning his name tag. “Aw shoot, I didn’t even introduce myself!” Dean realised, “I’m Dean. And you are?” He raised an eyebrow. “(Y/N).”

“Well nice to meet you (Y/N).” He grinned. “Hey how bout I give you my number, we can meet up sometime if you want.” He offered. “Okay, nice meeting you too.” You giggled, taking the slip of paper from his hands. “Thanks Dean, I’ll see you later!” You waved goodbye to him after paying and exited the story, leaving him grinning like an idiot.

Dean sat staring at his phone, anticipating the moment it’ll buzz to life and display your name on the caller ID. His shift ended 2 hours ago, but he’d heard nothing from you so far. Stupid, you didn’t tell him to call today. You’ve just met each other after all. Regardless, he wanted to hear your voice again. Right after that thought, a series of rings sounded out and your name flashed across his screen. He swiped right, trying to suppress the grin on his lips. “Hey (Y/N).” He greeted. “Hi Dean.” You giggled. Such a precious sound. “What are you up to?” Dean asked, flopping down on his bed. “Nothing much,” (Y/N) murmured, “just showered. You?” 

“I’m talking to you, duh.”   
“Other than that.” You rolled your eyes. “Nothing, really. I was waiting for you to call. You took your time.” Dean pouted to himself. “Sorry,” you sighed, “I just had to gather up the nerve.” This caught Dean’s attention. “Nerve for what?” You could almost face palm at his ignorance. “Um hello? It’s not everyday some cute guy at the shops gives you his number. How do you expect me to react?” Dean smirked on the other end. “So... You think I’m cute?” His voice laced with cockiness. “Yes, of course I do idiot. How could I not?” It was your turn to pout. “Aw, I’m glad you think so sugar. The feeling’s mutual.” He chuckled. “Sugar?” You cringed, “that’s a terrible petname. Try again.” 

“Okay,” Dean thought for a bit, “how about baby boy.” You gulped, feeling heat rise to your cheeks. “Better. Much better.” There was silence on the other end before Dean spoke up. “You know baby boy, I find it hard to believe guys haven’t tried to give you their number. No way a cute little thing like you has difficulty with romance.” You hummed. “Okay maybe I exaggerated just a little. Wanted to make you feel special.” You fiddled with your shirt, liking the way this conversation was going. “You do make me feel special, sweetheart. I’m so lucky that you even gave me a chance. However,” he paused, “you still lied to me. I don’t like liars.”

Your heart sped up hearing the drop in his voice, and a flame of arousal burned at the pit of your stomach. “I was just kidding around, Dean. It’s no big deal.” He ignored you. “Only bad boys lie. And you know what bad boys deserve? Punishment.” He licked his lips. You whimpered, feeling your pants become uncomfortably tight. “You know if you were here I’d bend you over my lap and spank your pretty ass raw, mark you up so well. You’d look so pretty baby, covered in my handprints. You’d like that wouldn’t you, slut.” You whined at the filthy promises, grinding your hips down on the mattress in search of any kind of friction. “Dean, please...” You hear him growl, the sound sending shivers down your spine. “That’s daddy to you slut.”

“Daddy! I need you!” Dean groaned, placing a hand on his aching crotch. “Touch yourself babyboy. Touch your pretty little cock for me. Fuck yourself open.” You quickly discarded your pants and boxers, gasping when the cool air hit your cock. There’s a shuffle as you retrieve the lube from your drawer. “Do you know what flavour this is, daddy?” Dean hears the click of a bottle cap being undone. “It’s peach. You like peaches?” You get a moan in response. “It’ll leave me tasting so good. Wish you were here to take a bite.” You relaxed against the pillows, spreading your legs for access. You circled your entrance, leaving a wet squelch. “I’m putting the first one in.” You said. Dean’s mind was so hazy with arousal that he could hardly process your words. 

The intrusion didn’t hurt, but it wasn’t pleasurable just yet. You slid in your index, biting you lip at the stretch. Moving your other hand to your cock, you found a decent rhythm to work with. Your gaze became blurry and you couldn’t hold in the noises as the pleasure began to take over. Dean wasn’t any better, his hand working up and down his girth. He couldn’t get enough of your pretty moans. He could only imagine how you looked, all flushed and sweaty, back arching beautifully while working yourself to an orgasm. “Tell daddy how it feels.” He grunted. 

“F-Feels so good. Wish it was you instea- AH!” White spots painted your vision as you struck that bundle of nerves inside you, pleasure filling your senses. Sliding in two more fingers, you aimed to hit that spot with every thrust. “D-Does daddy feel good?” You mewled. “Daddy feels so good babyboy, you’re doing so well. So good for me. My obedient little angel, hm? Wanna wreck you so badly. Wanna turn you into a whore that worships my cock, would you like that? Being my little cockslut? Of course you would, baby. I’ll make you feel so good. You can’t get enough of me. You can’t even wrap your whole hand around it, slut.” 

“D-Daddy... I don’t know how long I can, ngh, continue,” you panted, “I’m close!” Dean groaned, “me too baby. Cum for me sweetheart.” You came with an earth shattering cry, painting the sheets in white. You heard Dean grunt one last time before silence fell on both ends.

“That was fun.” Dean grinned. “It was.” You sighed in content. “Hey listen- I’m sorry if I got too carried away with the stuff I said. I tend to get a little heated in the moment.” He apologised. “Don’t worry! I actually enjoyed it. It was hot.” You smirked. “Dirty boy.” Dean snickered. “But I wanted to ask if you wanted to go to Luke’s tomorrow?” You smiled, slipping on an oversized hoodie. “I’d love to. It’s getting late though. I’ll see you then, okay? Goodnight.” You said softly. “Sure thing, (Y/N). Goodnight. Sweet dreams, beautiful.”


	2. 34 + 35

**Summary for the Chapter:**

> Can you stay up all night? (All night)  
> Fuck me 'til the daylight (daylight)  
> 34, 35 (yeah, yeah, yeah, yeah, 35, babe)  
> Can you stay up all night? (Can you stay?)  
> Fuck me 'til the daylight (can you stay?)  
> 34, 35 (yeah, yeah, yeah, yeah)  
> Oh-yeah-yeah

The warm, bitter taste of coffee enveloped your lips as you gazed out the window of Luke’s, admiring the sun setting in the distance. Dean should be here any second now. You gasped when two large hands covered your eyes and your vision went black, panic coursing through your veins before you heard that laugh you were now familiar with. “Hey sweetie.” Dean chuckled. “Dean! That wasn’t funny.” You whined, “You scared me.”

“Sorry pumpkin.” He grinned, “I’ll be right back, okay? I’m gonna go order. You want anything else?” You thought for a sec. “I’ll have a blueberry muffin.” He nodded, going up to the countertop. Your thoughts drifted back to last night. Butterflies filled your stomach when you remembered the things he said to you, how dominant he was. You hadn’t expected to do something sexual so fast, but you definitely didn’t regret it. Your thoughts were cut off by Dean placing a plate in front of you. “What’s on your mind?” He asked, noticing your expression. “This is our real first date.” You smiled. “It is.” he hummed. “But (Y/N), what happened last night- I don’t regret it.”

“Neither do I.” He reached over and took your hand in his, entwining his fingers with yours. There was a notable size difference between you two, but your palms fit together so well. It felt right. “But I don’t want you think we’re only gonna have sex,” he continued, “I really like you (Y/N). I wanna take you out on dates, get to know you.” He squeezes your hand gently, bringing it up to his lips and placing a gentle kiss on your knuckles. “I want that too, Dean.” You leaned closer. “So tell me everything about yourself, don’t leave anything out!”

After finishing your food, Dean offered to go back to his place and watch a movie and order some pizza, which you of course accepted. The two of you had been chatting for so long that you hadn’t noticed how dark it was outside until Luke said it was closing time. 

Now you were seated on his couch, scrolling through the ‘movies’ tab on Netflix. Dean wasn’t big on horror movies, but you lived for them. Dean returned from the kitchen with two big bowls on candy and chips. “So we’ve got blankets, snacks and pizza’s been ordered. Only thing left is the movie.” He said. “How about The Shining?” You suggested. His face paled. “Scared, Dean?” You snickered. You weren’t gonna force him to watch it if he didn’t want to but you had to admit the idea of him clinging to you for two hours seemed too appealing to pass up. “It’s okay, you can hold onto me if you’re scared.” You kissed his cheek, causing him to sulk but he didn’t protest. 

You noticed Dean was on the other end of the couch keeping a good distance between you two. “You’re so far away.” You pouted, making grabby hands at him. “Cuddle me.” He chuckled, finding you absolutely adorable. How could he turn that down? Shuffling closer, he brought you to his embrace so your head was tucked into the crook of his neck and your arms around his torso. Dean was concentrated on the screen, but your mind was only focused on his warmth and how fucking good he smelt. The scent of pine with a slight musk to it. You sighed, nuzzling his skin in content. He gently carded his hands through your hair, placing kisses on the top of your head. Dean was a lot more affectionate than your past boyfriends, which only made you fall for him harder.

Despite the jumpscares on the screen, you felt safe in his arms. You pulled back a little to look at him properly. His eyes were straight ahead, colours dancing on his face from the dimmed lights. You observed every last detail; his moles, the crinkle in his eyes, his dimples. It made you wonder how you got so lucky. Dean must have countless girls and boys chasing after him, but he chose you. It made your chest swell with warmth. 

“(Y/N), the movie’s that way.” He laughed, snapping you out of it. You blushed, averting your eyes but Dean grabbed your chin, tilting your head so you’d look him in the eyes. He leaned in, pressing your lips together. They tasted better than you imagined. And god, he was a good kisser. 

His tongue swiped your bottom lip, asking for entrance. You decided to play with him a little and denied him. His hand moved down south, giving your ass a squeeze causing you to gasp. He took his chance and before you knew it, you two were fighting for dominance. He won easily and took control of the kiss, placing you on his lap. 

The two of you broke apart, leaving you panting. You tilted your head back, giving him access to your neck as he ducked his head under. Your skin was smooth and unmarked, his own personal canvas to paint in purple and red. He was gonna shower with marks so you could show everyone who you belonged to. “Don’t bite me.” You warned, but it fell upon deaf ears. Dean was too busy placing open mouth kisses on your neck and sucking the skin until it was pink. You grind down on him desperately, wanting more. He growled and picked you up with little to no effort, heading for the bedroom.

He threw you on the bed like a rag doll, quickly discarding his shirt. Rough. You liked it. Once both of you were undressed, you took a moment to take each other in. Dean was built like a Greek god. So broad, with rippling muscles and bulging biceps. Your eyes trailed down to his defined v-line, to what was in between. Your eyes widened at the sight. He was big, roughly twelve inches. And thick. He was right, you wouldn’t be able to wrap your hand around it. Dean eyed you hungrily, from your rosy nipples to your slim waist. He crawled on top of you, licking his lips. “Get ready, sweetheart, I’m not going easy on you. You won’t be able to walk for a week.” He whispered hotly, trailing wet kisses from your collarbone to your navel.

He kissed your stomach, nuzzling the skin gently. “You’re so beautiful.” Heat rose to your cheeks. “You mean it?” You didn’t think your body was anything special, but to Dean you were the most gorgeous person he’d ever laid eyes on. “I mean it. You’re perfect.” He continued moving down, until you felt a tongue prodding your entrance. “Turn around for me sweetheart.” You obeyed, turning on your stomach so your head was in the pillows and ass in the air. Dean trailed a finger down your back before spreading your cheeks. He licked around your entrance, not quite going inside where you needed him the most. “Dean... Don’t tease me.” You whined, followed by a pained yelp as a slap echoed in the room. “What’d you call me?” Dean pulled back a little. “Sorry daddy.” 

“Don’t forget again.” He spanked you again on the other cheek, liking the way it jiggled after. He went back your hole, sucking insistently on the rim. He then dipped his tongue inside, dragging it along your walls savouring the flavour. You tasted so fucking good, Dean lapped at you like a starved man eating his last meal. 

He pulled away eventually, much to your dismay. “Tastes like candy.” He said. You buried your head further into the pillows from embarrassment. “It’s your turn, daddy.” You sat upright facing him on your knees. You crawled closer to him on all fours until you were face to face with his leaking length. Fuck, it looked even better up close. Your mouth watered. You imagined how it would feel inside you, filling you up so well. But you’d find out later. 

You swiped your thumb over the slit, collecting the precum leaking out. The two of you made eye contact as you brought your fingers to your lips, licking them clean. Dean moaned at the sight. You dragged your hand from the tip to the base, finding a steady rhythm. You had a feeling you’ll end up with a sore wrist after this. Dean was having the time of his life, head thrown back and eyes closed in bliss. Your hand was replaced with your mouth, sucking insistently, bobbing your head in time. “You don’t have to take all of it.” He reassured. You relaxed a little and used your hand for what you couldn’t reach, focusing on making him feel good. 

His hands gripped your hair and his hips gently bucked into your warm mouth, careful not to hurt you. “(Y/N) I’m gonna-” You felt a thick, salty taste in your mouth. Your first instinct was to spit it out, but Dean wouldn’t let you pull back. “Swallow babyboy. Don’t waste one drop.” Once again you obeyed, letting the hot liquid trickle down your throat. 

“Now to the fun part.” He smirked. You got on your hands, knowing what’s coming. “Do you have lube?” He asked. “In my back pocket.” You replied. “Damn (Y/N), you had this with you the whole time? I knew you were a slut, but this is different. Appreciate you being prepared though.” he placed a kiss to your temple. You hadn’t realised how long his fingers were until they were tracing up and down your crack, circling your tight entrance. He dipped a finger in, biting back a moan at the way you clenched around him, trying to keep him in, aching for more. One turned into three, thrusting at you in a rough pace trying to find the spot that would make you see stars. 

Suddenly you convulsed, your body jumping up from the intensity of the feeling, Dean holding you down. “Found it.” He said smugly. At this point you were having trouble holding your moans in, his fingers drilling into you at such a fast rate. His hand clapped around your mouth, muffling your whimpers. “Now now baby. You’re gonna wake up the whole neighbourhood. Do you want everyone on this street to know what a slut you are, how good you’re taking me? I bet you’d love that, whore.” A particularly harsh thrust to your prostate. “But I’m the only one that gets to hear your sweet moans. I’m the only one that’s allowed to see you like. Mine mine mine.” Your muscles tensed and thighs shook, signalling your orgasm was near.

Just like that he pulled away, admiring your hole clenching around nothing, leaving you whining in frustration. “Shut up, slut. We’re getting to the best part. Daddy’s gonna give you his cock and you’ll take it like a good boy.” He slapped your ass again and proceeded to slick up his cock. You turned on your back. You wanted to feel his whole body on you, skin on skin, his abs rubbing your stomach. You wanted to hear his moans in your ear, see his cock going in and out of you. 

“Ready babyboy?” He asked, lining himself up with your entrance. You nodded. Dean wasn’t satisfied with that, he slapped your thigh lightly. “Words babyboy. Tell me how much you want it. Tell me how much your slutty hole’s aching for this cock.” You flushed. As much as you valued your pride, you really wanted to be stuffed full and fucked senseless. “Please daddy, s-stuff me with your cock, destroy my insides! I’ve been a good boy for you haven’t I? Doesn’t babyboy deserve a reward? W-Wanna feel you, pretty please.” Tears threatened to pour down your cheeks.

He bottomed out in one thrust, staying put and letting you adjust. It hurt like a bitch. You were experienced, but you’d never taken someone as big as Dean. “You okay?” He asked, taking your hand in his. “Y-Yeah. Just give me a sec.” Thirty seconds passed with Dean placing butterfly kisses on your collarbone. “Move.” He starts thrusting immediately, gradually picking up the pace. Your mind fills with euphoria. The drag of his cock inside you felt delicious.

The feeling was overwhelming. There was just so much of Dean. You could feel him everywhere, penetrating the deepest parts of your body. The sound of skin slapping skin and the obscene squelch of lube filled the room, along with your high pitch moans. The bed was shaking so much you’d think there was an earthquake in the house. Your little body shook from the force of his thrusts, Dean’s large hands keeping a bruising grip on your hips. 

He was absolutely crazy over you. The way your ass hugged his cock, never wanting him to leave, trying to keep it inside. He made a mental note to try cockwarming in the future. Your legs locked around his waist and arms wrapped around his shoulders. Now you really appreciated his broadness. He felt the signs of an orgasm coming, and knew you were the same when you clenched around him again. You both came at the same time, him filling you up and you spilling all over your stomach. Dean didn’t pull out, but leaned closer to your cheeks were touching, panting while you closed your eyes trying to calm down. You hummed in satisfaction as Dean nuzzled you and kissed both your cheeks, rubbing your noses together. 

As soon as you thought he was gonna pull out, he flipped you over so he was laying under you. “I- Dean wha-” Dean cut you off. “Oh baby, did you think we were done? No angel. I’m going to use you all night, making you cum over and over again till the daylight. Hope you’ve got enough energy for that. You’re my little cocksleeve, and you’re gonna do what daddy says.” He hesitated a bit, breaking his act. “Unless you’re tired. We can stop here if you want. I won’t continue if you don’t want me to, it’s all up to you (Y/N).” Your heart fluttered knowing that under the dom exterior, he still cared about your comfort and what you wanted. “I want to, daddy.” You winked at him. “That’s my boy,” he smirked, “now ride me, babyboy.”

The request surprised you, but you sat up on Dean’s stomach as he lay back and adjusted the pillows so he was comfy. Taking a deep breath, you lined his cock up with your hole and sank down all the way. You almost came looking at Dean’s expression. The man looked completely lost in pleasure, like he’d never experienced something better his whole life. You felt a bit smug knowing you were the reason why. You started bouncing, trying to hit your own prostate and also make Dean feel good. His hands found their way to your hips again, not guiding you, but just because he liked the feel of your skin under his fingers.

You rolled your hips experimentally, seeing how Dean would react. He let out a particularly loud moan and his grip on you tightened. He likes that. You roll your hips again, biting your lip as the burning in the pit of your stomach increases. You gather up all the energy you have left and start bouncing faster, chasing your orgasm. “Babyboy I’m gonna- ah fuck.” You mewled at the feeling of his cum painting your walls, leaking out slowly and making a mess. “You’re good at that.” He murmured, getting a tissue from the bedside table. “Thank you daddy.” 

Once you two were cleaned up, he flipped you over again so you were on all fours. He found it hot how you were so easy to manhandle, letting him do whatever he wanted to your body without protest. So fucking submissive. He really got lucky. “A-Ah...” You felt him enter you again, the slide was easy since your hole was gaping. “Your hole’s so loose slut, such a sloppy bitch. You like being used over and over huh, like being ready for me to use you whenever I want. My personal cum dump.” He gripped your hair harshly, tilting your head back while he fucked you, making you arch your back. A thread of unbroken moans left your lips at the rough pace, you could still feel the burn from the spankings everytime his skin made contact with yours. 

“Hm, I love you baby. Love you and your tight hole. You’re so, so perfect angel. The best babyboy. Daddy couldn’t have asked for anyone better.” His words brought you to yet another orgasm. He pulled out this time before he came, dirtying the sheets. You both agreed to take a break until the next round. It was going to be a long night, you needed to save your energy. So there you were, lying next to each other while Dean traced circles on your hip. The room reeked of sex but that was okay. It smelt like both of you. All you needed was each other.

**Author's Note:**

> This was requested by @//winchesterzforever on Tumblr. Hope you enjoyed!


End file.
